2-(Methylsulfanylphenylamino-methylene)malonic acid diethyl ester → 4-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester

HRID 1727463Notes

Reaction equation

HRID 1727463 reaction equation
C(O[C:4](=[O:21])[C:5](=[C:11]([S:19][CH3:20])[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>ClC1C=CC=CC=1Cl>[CH2:9]([O:8][C:6]([C:5]1[C:11]([S:19][CH3:20])=[N:12][C:13]2[C:14]([C:4]=1[OH:21])=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:7])[CH3:10]

Participants

3

Reactant 1

HCID 155029782-(Methylsulfanylphenylamino-methylene)malonic acid diethyl ester

Product 1

HCID 1784701074-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 2-(methylsulfanyl-phenylamino-methylene)-malonic acid diethyl ester (27 g, 87 mmol) in 1,2-dichlorobenzene (100 mL) was heated to reflux for 1.5 h. The solvent was removed under reduced pressure and the oily residue was triturated with hexane to afford a pale yellow solid that was purified by preparative HPLC to yield 4-hydroxy-2 -methylsulfanyl-quinoline-3-carboxylic acid ethyl ester (8 g, 35%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customThe solvent was removed under reduced pressure
  4. customthe oily residue was triturated with hexane
  5. customto afford a pale yellow solid
  6. customthat was purified by preparative HPLC

Sources & evidence

ORD record
ord-b8175f49b355461cacd0e7aba79d392d
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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